3-(3-chlorophenyl)isoxazol-5(4H)-one | 51725-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-chlorophenyl)isoxazol-5(4H)-one
• 英文别名: 3-(3-Chlorophenyl)-4,5-dihydro-1,2-oxazol-5-one；3-(3-chlorophenyl)-4H-1,2-oxazol-5-one
• CAS: 51725-85-0
• 化学式: C₉H₆ClNO₂
• mdl: MFCD11845106
• 分子量: 195.605
• InChiKey: BVAIGBCPSXKAMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-chlorophenyl)isoxazol-5(4H)-one 在 正丁基锂 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 生成 (3-Azepan-1-yl-propyl)-benzo[1,3]dioxol-5-ylmethyl-[3-(3-chloro-phenyl)-isoxazol-5-yl]-amine
  参考文献：
  名称：

  Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)

  摘要：

  The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50S of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00745-4
• 作为产物：
  描述：

  3-氯苯乙酮 在 盐酸羟胺 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 mineral oil 为溶剂， 生成 3-(3-chlorophenyl)isoxazol-5(4H)-one
  参考文献：
  名称：

  通过Rh催化级联C–H活化/环化3-芳基异恶唑酮与环2-重氮-1,3-二酮，构建异恶唑酮融合的菲啶

  摘要：

  描述了Rh（III）催化的3-芳基-5-异恶唑酮与环2-重氮-1,3-二酮的级联C–H活化/分子内环化，导致异恶唑[2,3- f ]的形成菲啶骨架。该协议的特征是同时一锅形成两个新的C–C / C–N键和一个杂环，具有中等至良好的产率，并具有良好的官能团相容性。适于大规模合成和进一步转化。

  DOI：

  10.1039/d0ob02310h

文献信息

• Palladium Catalyzed Insertion Reaction of Isocyanides with 3-Arylisoxazol-5(4<i>H</i>)-ones: Synthesis of 4-Aminomethylidene Isoxazolone Derivates
  作者：Yi-Ming Zhu、Pei Xu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1021/acs.joc.9b01585

  日期：2019.9.6

  A palladium catalyzed insert reaction of isocyanides to 3-arylisoxazol-5(4H)-ones for the construction of 4-aminomethylidene isoxazolone derivates is reported. In this transformation, only the C–H bond of the methylene group was involved while the remaining ring structure was retained. In general, this work provided a new protocol for the synthesis of 4-aminomethylidene isoxazolones.

  报道了钯催化的异氰酸酯与3-芳基异恶唑-5（4 H）-的插入反应，用于构建4-氨基亚甲基异恶唑酮衍生物。在这种转变中，仅涉及亚甲基的C–H键，而保留了其余的环结构。通常，这项工作为4-氨基亚甲基异恶唑酮的合成提供了新的协议。
• Chromow; Porai-Koschiz, Zhurnal Obshchei Khimii, 1947, vol. 17, p. 1816,1824
  作者：Chromow、Porai-Koschiz

  DOI：——

  日期：——
• Szeimies,G. et al., Chemische Berichte, 1977, vol. 110, p. 2922 - 2938
  作者：Szeimies,G. et al.

  DOI：——

  日期：——
• Construction of isoxazolone-fused phenanthridines <i>via</i> Rh-catalyzed cascade C–H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones
  作者：Wangcheng Hu、Xinwei He、Tongtong Zhou、Youpeng Zuo、Shiwen Zhang、Tingting Yang、Yongjia Shang

  DOI：10.1039/d0ob02310h

  日期：——

  A Rh(III)-catalyzed cascade C–H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C–C/C–N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to

  描述了Rh（III）催化的3-芳基-5-异恶唑酮与环2-重氮-1,3-二酮的级联C–H活化/分子内环化，导致异恶唑[2,3- f ]的形成菲啶骨架。该协议的特征是同时一锅形成两个新的C–C / C–N键和一个杂环，具有中等至良好的产率，并具有良好的官能团相容性。适于大规模合成和进一步转化。
• Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)
  作者：Philippe G Nantermet、James C Barrow、George F Lundell、Janetta M Pellicore、Kenneth E Rittle、MaryBeth Young、Roger M Freidinger、Thomas M Connolly、Cindra Condra、Jerzy Karczewski、Rodney A Bednar、Stanley L Gaul、Robert J Gould、Kris Prendergast、Harold G Selnick

  DOI：10.1016/s0960-894x(01)00745-4

  日期：2002.2

  The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50S of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min. (C) 2002 Published by Elsevier Science Ltd.